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MetaCyc Pathway: chrysophanol biosynthesis
Inferred from experiment

Pathway diagram: chrysophanol biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisQuinone Secondary Metabolites Biosynthesis

Some taxa known to possess this pathway include : Setophoma sacchari

Expected Taxonomic Range: Eukaryota

Emodin appears to be produced from acetyl-CoA and malonyl-CoA [Zobayed06], though specifics of this biosynthesis have not been published. Emodin is an intermediate in secalonic acid production [Kurobane79, Zeng04], which has been isolated from fungi and implicated as a phytoxic substance that weakens plant defenses and increases susceptibility to fungal pathogens. Anthraquinones, such as chrysophanol and emodin, are also toxic substances found in a range of fungal and plant species [Anderson86, Mueller99]. In plants, these compounds appear to function in defense [Shen02].

Citations: [Anderson88b]

Created 09-Oct-2006 by Walk T, TAIR


Anderson86: Anderson JA (1986). "Conversion of emodin to chrysophanol in a cell-free system from Pyrenochaeta terrestris." Phytochemistry 25:103-106.

Anderson88b: Anderson JA, Lin BK, Williams HJ, Scott AI (1988). "Deoxygenation of phenolic natural products. Enzymatic conversion of emodin to chrysophanol." Journal of the American Chemical Society 110:1624-1626.

Kurobane79: Kurobane I, Vining LC, McInnes AG (1979). "Biosynthetic relationships among the secalonic acids. Isolation of emodin, endocrocin and secalonic acids from Pyrenochaeta terrestris and Aspergillus aculeatus." J Antibiot (Tokyo) 32(12);1256-66. PMID: 541252

Mueller99: Mueller SO, Schmitt M, Dekant W, Stopper H, Schlatter J, Schreier P, Lutz WK (1999). "Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants." Food Chem Toxicol 37(5);481-91. PMID: 10456676

Shen02: Shen Z, Li J, Hu Z (2002). "[Distribution of anthraquinones in leaves of two Aloe species and their defence strategy]." Ying Yong Sheng Tai Xue Bao 13(11);1381-4. PMID: 12624988

Zeng04: Zeng R, Luo S, Shi Y (2004). "[Allelopathic effects of secalonic acid F produced by Aspergillus japonicus on Zea mays]." Ying Yong Sheng Tai Xue Bao 15(1);145-8. PMID: 15139208

Zobayed06: Zobayed SM, Afreen F, Goto E, Kozai T (2006). "Plant-Environment Interactions: Accumulation of Hypericin in Dark Glands of Hypericum perforatum." Ann Bot (Lond) 98(4);793-804. PMID: 16891333

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sun May 1, 2016, biocyc14.